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    Chemistry

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    Also known as: 609799-22-6, Hetlioz, Vec-162, Bms-214778, Vec 162, Bms 214778
    Molecular Formula
    C15H19NO2
    Molecular Weight
    245.32  g/mol
    InChI Key
    PTOIAAWZLUQTIO-GXFFZTMASA-N
    FDA UNII
    SHS4PU80D9
    Tasimelteon
    Tasimelteon is a selective dual melatonin receptor agonist indicated for the treatment of Non-24-Hour Sleep-Wake Disorder (N24HSWD). Occurring commonly in blind individuals without light perception, this condition is often characterized by periods of night-time insomnia and day-time sleepiness. In blind individuals, a lack of light stimulation causes an extension of the 24-hour circadian cycle and can lead to progressively delayed sleep onset. By activating melatonin receptors MT1 and MT2 in the suprachiasmatic nucleus of the brain, tasimelteon has been shown to improve sleep by resynchronizing the circadian rhythm through its "non-photic" mechanism. Tasimelteon is currently the only drug available for the treatment of N24HSWD and was granted orphan drug status by the FDA in 2010.
    Tasimelteon is a Melatonin Receptor Agonist. The mechanism of action of tasimelteon is as a Melatonin Receptor Agonist.
    1 2D Structure

    Tasimelteon

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-[[(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methyl]propanamide
    2.1.2 InChI
    InChI=1S/C15H19NO2/c1-2-15(17)16-9-10-8-13(10)11-4-3-5-14-12(11)6-7-18-14/h3-5,10,13H,2,6-9H2,1H3,(H,16,17)/t10-,13+/m0/s1
    2.1.3 InChI Key
    PTOIAAWZLUQTIO-GXFFZTMASA-N
    2.1.4 Canonical SMILES
    CCC(=O)NCC1CC1C2=C3CCOC3=CC=C2
    2.1.5 Isomeric SMILES
    CCC(=O)NC[C@@H]1C[C@H]1C2=C3CCOC3=CC=C2
    2.2 Other Identifiers
    2.2.1 UNII
    SHS4PU80D9
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Bms 214778

    2. Bms-214778

    3. Bms214778

    4. N-((2-(2,3-dihydro-4-benzofuranyl)cyclopropyl)methyl)propanamide

    2.3.2 Depositor-Supplied Synonyms

    1. 609799-22-6

    2. Hetlioz

    3. Vec-162

    4. Bms-214778

    5. Vec 162

    6. Bms 214778

    7. Shs4pu80d9

    8. Chebi:79042

    9. Bms214778

    10. Bms-214,778

    11. N-(((1r,2r)-2-(2,3-dihydrobenzofuran-4-yl)cyclopropyl)methyl)propionamide

    12. N-[[(1r,2r)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methyl]propanamide

    13. N-{[(1r,2r)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methyl}propanamide

    14. N-(((1r,2r)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl)methyl)propanamide

    15. Propanamide, N-(((1r,2r)-2-(2,3-dihydro-4-benzofuranyl)cyclopropyl)methyl)-

    16. Tasimelteon [usan]

    17. Tasimelteon [usan:inn]

    18. Unii-shs4pu80d9

    19. Tasimelteonum

    20. N-([(1r,2r)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methyl)propanamide

    21. Hetlioz (tn)

    22. Hetlioz Lq

    23. Tasimelteon [mi]

    24. Tasimelteon [inn]

    25. Tasimelteon (usan/inn)

    26. Tasimelteon [vandf]

    27. Tasimelteon [mart.]

    28. Tasimelteon [who-dd]

    29. Gtpl7393

    30. Schembl3505912

    31. Chembl2103822

    32. Tasimelteon, >=98% (hplc)

    33. Amy6925

    34. Dtxsid70209826

    35. Tasimelteon [orange Book]

    36. Hms3885l17

    37. Act06729

    38. Bcp07180

    39. Ex-a2729

    40. Zinc4392649

    41. Mfcd09033789

    42. S4281

    43. Akos025149360

    44. Ac-6143

    45. Ccg-266915

    46. Cs-5512

    47. Db09071

    48. Ncgc00522560-01

    49. As-35291

    50. Hy-14803

    51. T3813

    52. J3.640.465e

    53. D09388

    54. 799t226

    55. Q7687250

    56. N-((2-(2,3-dihydro-4-benzofuranyl)cyclopropyl)methyl)propanamide

    57. (trans)-n-[[2-(2,3-dihydrobenzofuran-4-yl) Cyclopropyl]methyl]propanamide

    58. (trans)-n-[[2-(2,3-dihydrobenzofuran-4-yl)cyclopropyl]methyl]propanamide

    59. (-)-(trans)-n-[[2-(2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl] Methyl]propanamide

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 245.32 g/mol
    Molecular Formula C15H19NO2
    XLogP32.2
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count4
    Exact Mass245.141578849 g/mol
    Monoisotopic Mass245.141578849 g/mol
    Topological Polar Surface Area38.3 Ų
    Heavy Atom Count18
    Formal Charge0
    Complexity318
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameHetlioz
    PubMed HealthTasimelteon (By mouth)
    Drug ClassesCentral Nervous System Agent
    Drug LabelHETLIOZ (tasimelteon) is a melatonin receptor agonist, chemically designated as (1R, 2R)-N-[2-(2,3-dihydrobenzofuran-4-yl)cyclopropylmethyl]propanamide, containing two chiral centers. The molecular formula is C15H19NO2, and the molecular weight is 24...
    Active IngredientTasimelteon
    Dosage FormCapsule
    RouteOral
    Strength20mg
    Market StatusPrescription
    CompanyVanda Pharms

    2 of 2  
    Drug NameHetlioz
    PubMed HealthTasimelteon (By mouth)
    Drug ClassesCentral Nervous System Agent
    Drug LabelHETLIOZ (tasimelteon) is a melatonin receptor agonist, chemically designated as (1R, 2R)-N-[2-(2,3-dihydrobenzofuran-4-yl)cyclopropylmethyl]propanamide, containing two chiral centers. The molecular formula is C15H19NO2, and the molecular weight is 24...
    Active IngredientTasimelteon
    Dosage FormCapsule
    RouteOral
    Strength20mg
    Market StatusPrescription
    CompanyVanda Pharms

    4.2 Drug Indication

    Tasimelteon is indicated for the treatment of Non-24-Hour Sleep-Wake Disorder (N24HSWD).

    FDA Label

    Hetlioz is indicated for the treatment of Non-24-Hour Sleep-Wake Disorder (Non-24) in totally blind adults.

    5 Pharmacology and Biochemistry
    5.1 FDA Pharmacological Classification
    5.1.1 Active Moiety
    TASIMELTEON
    5.1.2 FDA UNII
    SHS4PU80D9
    5.1.3 Pharmacological Classes
    Melatonin Receptor Agonists [MoA]; Melatonin Receptor Agonist [EPC]
    5.2 ATC Code

    N05CH

    N - Nervous system

    N05 - Psycholeptics

    N05C - Hypnotics and sedatives

    N05CH - Melatonin receptor agonists

    N05CH03 - Tasimelteon

    5.3 Absorption, Distribution and Excretion

    Route of Elimination

    Following oral administration of radiolabeled tasimelteon, 80% of total radioactivity was excreted in urine and approximately 4% in feces, resulting in a mean recovery of 84%. Less than 1% of the dose was excreted in urine as the parent compound.

    Volume of Distribution

    The apparent oral volume of distribution of tasimelteon at steady state in young healthy subjects is approximately 56 - 126 L.

    5.4 Metabolism/Metabolites

    Tasimelteon is extensively metabolized. Metabolism of tasimelteon consists primarily of oxidation at multiple sites and oxidative dealkylation resulting in opening of the dihydrofuran ring followed by further oxidation to give a carboxylic acid. CYP1A2 and CYP3A4 are the major isozymes involved in the metabolism of tasimelteon. Phenolic glucuronidation is the major phase II metabolic route.

    5.5 Biological Half-Life

    The observed mean elimination half-life for tasimelteon is 1.3 0.4 hours.

    5.6 Mechanism of Action

    Tasimelteon is a selective dual agonist of the melatonin receptors MT1 and MT2.

    API Reference Price

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    13-Jan-2023
    10-Sep-2024
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